✍ Scribed by Zejun Xiao; Jack W. Timberlake
No coin nor oath required. For personal study only.
We studied the nucleophilic addition of organocerium reagents to ␣-alkoxy hydrazones. The results depend upon the organocerium reagents, the nature of protection for the hydroxy group, and the solvents used. Contrary to Grignard reagents, organocerium reagents derived from Grignard reagents effectively add to ␣-alkoxy hydrazones. In addition, a new type of elimination reaction of ␣-alkoxy hydrazones to the corresponding nitriles by methyl chloroformate was found. This methodology is an efficient and potentially practical synthetic route to b-hydroxy amines.
📜 SIMILAR VOLUMES
Asymmetric Addition of Organometallic Reagents to Chiral α-Alkoxy Hydrazones. -The diastereoselective addition of three different types of nucleophilic reagents to three different α-alkoxy hydrazones is studied. With exception of the reation of the silylated hydrazone (Ib) with the heterogeneous 1: